| 97% |
With oxygen In dimethyl sulfoxide at 100℃; for 1.5h; |
|
| 95% |
With 1,4-diaza-bicyclo[2.2.2]octane; air In acetonitrile at 20℃; for 30h; |
|
| 95% |
With copper(l) iodide; triethylamine; triphenylphosphine In acetonitrile at 25℃; for 24h; |
|
| 95% |
With oxygen In N,N-dimethyl-formamide at 120℃; for 3h; |
|
| 94% |
With copper(l) iodide; 4-(1,2,5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranos-3-yl)-1H-[1,2,3]-triazole; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; |
|
| 92% |
With 1,10-Phenanthroline; tetrabutylammonium acetate; acetic acid In acetonitrile at 20℃; Electrochemical reaction; |
|
| 91% |
With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(l) chloride In 1,1,1,3,3-pentafluorobutane at 20℃; for 24h; |
|
| 91% |
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; oxygen In acetonitrile at 50℃; |
|
| 90% |
With N-Bromosuccinimide; copper(l) iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 4h; |
|
| 90% |
With oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride In tetrahydrofuran at 20℃; for 24h; Air atmosphere; |
|
| 90% |
With copper(l) iodide; 1-(2-ethoxy-2-oxoethyl)-1-methyl-pyrrolidinium nonafluorobutanesulfonate; triethylamine at 20℃; for 3h; |
Typical procedure for the Glaser coupling
General procedure: Phenyl acetylene (2 mmol), CuI (5 mol%), TEA (1 mmol) and IL (1 g) were added in a 25 mL round bottom flask and stirred under aerobic conditions at RT for 2 h. Progress of reaction was monitored by thin layer chromatography (TLC) using aluminum backed silica gel 60 (F254) plates. The desired product was isolated from reaction mixture by extracting with diethyl ether (2×10 mL). The product obtained after evaporation of the solvent was purified by column chromatography (silica mesh size 60-120) and eluted with n-hexane to afford pure symmetrical 1,3-diyne. |
| 89% |
With copper(l) iodide; air; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 31h; |
|
| 89.7% |
With oxygen In diethyl ether |
|
| 88% |
With trimethylamine-N-oxide; sodium acetate; palladium dichloride In acetonitrile at 20℃; for 13h; |
|
| 88% |
With copper(l) iodide; nickel(II) chloride hexahydrate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique; |
|
| 86% |
With pyridine; C20H28ClCuN5O2(1+)*Br(1-) In water at 20℃; for 24h; |
|
| 85% |
With piperidine In dichloromethane at 20℃; for 6h; |
2.4 General Procedure for the Homocouplingof Alkynes Catalysed by Cu(0)-NPs-PANI
General procedure: To a stirred solution of alkynes (1 mmol) in dichloromethaneat room temperature and open air, the catalyst (20 mg,0.05 mol%) was added. Then the diluted solution of piperidine(30 mol%) in dichloromethane was added drop wise.The reaction was continued at room temperature and monitoredby TLC. Once the reaction was complete, the reactionmixture was filtered and diluted by addition of 25 mlof dichloromethane to the reaction mixture. The reactionmixture was washed with 0.1 N HCl (2 × 25 ml) followed bywashing with water (2 × 25 ml) and brine (25 ml). The crudeproduct was isolated and purified by column chromatographyusing hexane/ethyl acetate as eluent. The products werecharacterised by 1H and 13C NMR spectroscopy. |
| 83% |
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; triethylamine In acetone at 20℃; for 20h; |
|
| 82% |
With piperidine In various solvent(s) at 25℃; for 8h; |
|
| 82% |
With oxygen In benzonitrile at 99.84℃; for 4h; |
|
| 82% |
With oxygen In benzonitrile at 99.84℃; for 4h; |
|
| 82% |
With oxygen In benzonitrile at 100℃; for 4h; |
|
| 78% |
With piperidine In dichloromethane at 25℃; for 3h; |
|
| 78% |
With oxygen In dimethyl sulfoxide at 80℃; for 0.75h; Green chemistry; |
General procedure for alkyne homocoupling
General procedure: To a solution of terminal alkyne (0.3 mmol) in DMSO (3 mL) was added 5 mol% Cu(II)-clay in a two-neck round bottom flask. A condenser was attached to one neck of this flask, whereas the other neck was closed with a rubber septum. Oxygen was bubbled through a needle inserted through the septum. The resulting mixture was refluxed for the required duration. The reaction was cooled at room temperature and the products were extracted with dichloromethane. The combined organic layers were dried with anhydrous MgSO4, filtered off, and concentrated in vacuo to obtain the crude products, which were purified by silica-gel chromatography to afford the corresponding product. |
| 78% |
With copper(l) iodide; perfluorobutanesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform at 20℃; for 0.166667h; |
|
| 76% |
With piperidine In tetrahydrofuran at 65℃; for 24h; |
|
| 75% |
Stage #1: 1-Ethynylcyclohexan-1-ol With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.5h; Inert atmosphere;
Stage #2: With 1-acetoxy-1,2-benziodoxol-3-one In tetrahydrofuran; hexane at -40 - 20℃; for 2h; Inert atmosphere; |
General procedure for the dimerization of terminal alkynes
General procedure: A 1.6 M solution of n-BuLi in hexanes (1.1equiv) was added to a solution of the corresponding terminal alkyne (1.0 equiv) in THF (5 mL per mmol) at -40 °C. After stirring for 30min, acetoxy-benziodoxole 6 (1.1equiv) was added in one portion. The mixture was kept at -40 °C for 10 min and then allowed to reach room temperature while stirring for 2 h. Then, the reaction mixture was quenched with a saturated solution of NaHCO3 and extracted three times with dichloromethane. After the evaporation of the solvent, the crude product was purified by column chromatography (silica gel; heptanes/EtOAc) to afford the alkyne dimer 7, as well as 13-24, in the reported yields |
| 60% |
With Cu-modified hydroxyapatite; air In acetonitrile for 72h; Reflux; |
General procedure for homo-coupling of 1-8 alkynes
General procedure: Starting from alkynes 1-8 leads exclusively to the corresponding diynes 9-16 coupling compounds using the following conditions: The catalyst (60 mg, 15 mol %) is weighed into the flask, the solvent (6 mL CH3CN) is added. The alkyne (0.4 mmol) was dissolved in a small amount of solvent (CH3CN) and added to the mixture. The mixture is heated to reflux and air is bubbled through the solution. The reaction mixture was let to stir several hours (72 h). After filtration, the crude product was purified by column chromatography and identified by 1H NMR and 13C NMR spectra. |
| 53% |
With basolite C300; potassium carbonate In 1,4-dioxane at 85℃; for 24h; |
|
| 30% |
With 1,10-Phenanthroline; [bis(acetoxy)iodo]benzene In dichloromethane at 70℃; Sealed tube; Schlenk technique; |
2.6. Catalytic performance of SiO2/SSQ/Au
General procedure: The alkyne coupling reactions was performed in a sealed reactiontube charged with phenylacetylene (29 μL, 0.25 mmol), 1,10-phenanthroline(18 mg, 0.1 mmol), iodobenzene diacetate (80 mg, 0.25 mmol),gold catalyst (18 mg, 0.22 mol%) in dichloromethane (3 mL). The reactionmixture was stirred at 70 °C for 24 h. As dichloromethane wasused as solvent and the reaction was performed above its boiling pointin a sealed flask, hypervalent iodine was chosen instead of oxygen fromthe open atmosphere. The crude reaction mixture was purified bycolumn chromatography using hexane as eluent. All characterizationdata (1H NMR and 13C NMR spectra) of the organic compounds arepresented in Supplementary material (Figures S1-S17). |
|
With ethanol; ammonium chloride; copper(l) chloride at 30℃; weiteres Reagens: verd. wss. HCl; Einleiten von Luft in die Reaktionsloesung bei 70grad; |
|
|
With ethanol; ammonium chloride; copper(l) chloride weiteres Reagens: wss. HCl; anschliessendes Erwaermen mit wss. H2O2; |
|
|
With 1,4-diaza-bicyclo[2.2.2]octane at 140 - 170℃; for 0.5h; Microwave irradiation; |
|
| 54 %Spectr. |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In acetonitrile at 20℃; for 40h; |
|
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
HazMat Fee +
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
